Methyl Ethyl Ketone → HCID 86743108, compound

HRID 1904424Notes

Reaction equation

HRID 1904424 reaction equation
[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C(C)=O)C.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.[OH-].[Na+]>O>[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28]([OH:8])(=[O:30])=[O:29])=[CH:24][CH:23]=1.[C:1]1([C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 73974-Toluenesulfonyl chlorideHCID 8400BenzoinHCID 14798Sodium Hydroxide

Product 1

HCID 86743108HCID 86743108, compoundYield 175.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With stirring, 424.5 g (2.0 moles) of benzoin are added to 650 ml of methyl ethyl ketone in a 2.5 liter sulfonating flask. The resultant beige suspension is stirred for 5 minutes, then 400.4 g (2.1 moles) of pulverised p-toluenesulfonyl chloride are added. No chemical reaction takes place as yet. The temperature falls from room temperature to c. +5° C. When the addition is complete, the suspension is stirred for a further 5 minutes and then 50 ml of deionised water are added. Then 293.3 g of 30% aqueous sodium hydroxide solution (corresponding to 2.2 moles of NaOH) are added dropwise over 30 minutes, while keeping the temperature at 10°-15° C. by cooling with an ice bath. The beige suspension is efficiently stirred at this temperature for 6 hours, then cooled to -10° to -15° C. and vigorously further stirred for a further hour at this temperature. The beige crystal slurry, which is readily stirrable up to the end, is isolated by filtration, washed with 1 to 3×200 ml of deionised water and thereafter once with 150 ml of aqueous ice-cold methyl ethyl ketone, and dried under vacuum at room temperature, to give 674 g (92% of theory) of benzoin p-toluenesulfonate in the form of white crystals which melt at 99°-101° C. The purity of the product is at least 98% according to analysis by thin-layer chromatography and NMR spectroscopy. A sample stirred in water shows no acid reaction to litmus paper.

Workup

  1. stirringThe resultant beige suspension is stirred for 5 minutes
  2. customNo chemical reaction
  3. customfalls from room temperature to c
  4. custom+5° C
  5. additionWhen the addition
  6. stirringthe suspension is stirred for a further 5 minutes
  7. customat 10°-15° C.
  8. temperatureby cooling with an ice bath
  9. stirringThe beige suspension is efficiently stirred at this temperature for 6 hours
  10. temperaturecooled to -10° to -15° C.
  11. stirringvigorously further stirred for a further hour at this temperature
  12. customis isolated by filtration
  13. washwashed with 1 to 3×200 ml of deionised water
  14. dry with materialonce with 150 ml of aqueous ice-cold methyl ethyl ketone, and dried under vacuum at room temperature

Sources & evidence

ORD record
ord-9c21eb14cc0a4bbfa6fcde57f5cf5576
Source dataset
uspto-grants-1989_06
Patent number
US04837350

Reaction notes

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